Call us at (475) 244-9781 to learn more about active adult communities near Cheshire
Cheshire, CT 55+ active adult communities & homes for sale
125 communities near Cheshire
290 homes near Cheshire
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![Castle Heights of Cheshir...]()
$500Ks
- $600Ks
Castle Heights of Cheshir..., Cheshire, CT
Resale Only
|
55+ age-restricted
|
Built 2007 - 2022
|
88 homes
3 rating (2 reviews)
![Heritage Hills]()
$300Ks
- $900Ks
Heritage Hills, Somers, NY
Resale Only
|
Age-targeted
|
Built 1974 - 2006
|
2,600 homes
3.6 rating (7 reviews)
![Heritage Village]()
$100Ks
- $400Ks
Heritage Village, Southbury, CT
Resale Only
|
55+ age-restricted
|
Built 1967 - 2005
|
2,580 homes
No reviews yet
![Leisure Village]()
$200Ks
- $500Ks
Leisure Village, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1969 - 1986
|
1,500 homes
No reviews yet
![The Greens at Half Hollow]()
$600Ks
- $1Ms
The Greens at Half Hollow, Melville, NY
Resale Only
|
55+ age-restricted
|
Built 1994 - 2005
|
1,200 homes
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(475) 244-9781
No reviews yet
![Rivington]()
$500Ks
- $900Ks
Rivington, Danbury, CT
New and Resale
|
Age-targeted
|
Built 2006 - present
|
1,050 homes
4 rating (1 reviews)
![Jefferson Village]()
$200Ks
- $500Ks
Jefferson Village, Yorktown Heights, NY
Resale Only
|
55+ age-restricted
|
Built 1967 - 1982
|
1,000 homes
No reviews yet
![Oronoque Village]()
$300Ks
- $600Ks
Oronoque Village, Stratford, CT
Resale Only
|
55+ age-restricted
|
Built 1971 - 1977
|
929 homes
No reviews yet
![The Village at Oxford Gre...]()
$500Ks
- $700Ks
The Village at Oxford Gre..., Oxford, CT
New and Resale
|
55+ age-restricted
|
Built 2004 - present
|
835 homes
No reviews yet
![Meadowbrook Pointe Athlet...]()
$1Ms
- $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only
|
55+ age-restricted
|
Built 2015 - 2016
|
720 homes
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
No reviews yet
![Leisure Knoll]()
$200Ks
- $400Ks
Leisure Knoll, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1982
|
701 homes
No reviews yet
![Country Pointe Plainview]()
$1Ms
- $1Ms
Country Pointe Plainview, Plainview, NY
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
660 homes
5 rating (1 reviews)
![Fairfield at St. James]()
$400Ks
- $500Ks
Fairfield at St. James, St. James, NY
Resale Only
|
55+ age-restricted
|
Built 1972 - 1989
|
653 homes
No reviews yet
![Leisure Glen]()
$400Ks
- $500Ks
Leisure Glen, Ridge, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 2010
|
646 homes
No reviews yet
![Spring Lake Village]()
$200Ks
- $200Ks
Spring Lake Village, Southington, CT
Resale Only
|
55+ age-restricted
|
Built 1970 - 2004
|
640 homes
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(475) 244-9781
4 rating (8 reviews)
![Glenwood Village]()
$100Ks
- $400Ks
Glenwood Village, Riverhead, NY
New and Resale
|
55+ age-restricted
|
Built 1959 - present
|
588 homes
3.7 rating (3 reviews)
![Greenwood Village]()
$100Ks
- $200Ks
Greenwood Village, Manorville, NY
Resale Only
|
55+ age-restricted
|
Built 1980 - 2000
|
512 homes
No reviews yet
![The Seasons at East Meado...]()
$500Ks
- $600Ks
The Seasons at East Meado..., East Meadow, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2012
|
404 homes
No reviews yet
![Regency at Prospect]()
$400Ks
- $400Ks
Regency at Prospect, Prospect, CT
Resale Only
|
55+ age-restricted
|
Built 2006 - 2020
|
379 homes
No reviews yet
![Dutchgate]()
$400Ks
- $500Ks
Dutchgate, Valley Stream, NY
Resale Only
|
55+ age-restricted
|
Built 2009 - 2015
|
348 homes
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
No reviews yet
![The Waterways at Moriches]()
$400Ks
- $600Ks
The Waterways at Moriches, Moriches, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1999
|
343 homes
No reviews yet
![The Retreat at Carmel]()
$400Ks
- $600Ks
The Retreat at Carmel, Carmel, NY
Resale Only
|
55+ age-restricted
|
Built 2008 - 2018
|
312 homes
3.5 rating (2 reviews)
![Foxwood Village]()
$300Ks
- $400Ks
Foxwood Village, Calverton, NY
Resale Only
|
55+ age-restricted
|
Built 1986 - 2007
|
294 homes
1 rating (1 reviews)
![Plymouth Estates at Mount...]()
$500Ks
- $500Ks
Plymouth Estates at Mount..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2013
|
285 homes
4 rating (1 reviews)
![Vineyards at Blue Point]()
$800Ks
- $800Ks
Vineyards at Blue Point, Blue Point, NY
Resale Only
|
55+ age-restricted
|
Built 2016 - 2018
|
280 homes
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(475) 244-9781
4.6 rating (9 reviews)
![Meadowbrook Pointe Links ...]()
$300Ks
- $700Ks
Meadowbrook Pointe Links ..., Medford, NY
New and Resale
|
55+ age-restricted
|
Built 2010 - present
|
280 homes
No reviews yet
![HarborView]()
$900Ks
- $1Ms
HarborView, Port Washington, NY
Resale Only
|
55+ age-restricted
|
Built 2002 - 2004
|
270 homes
No reviews yet
![The Club at Melville]()
$500Ks
- $500Ks
The Club at Melville, Melville, NY
Resale Only
|
55+ age-restricted
|
Built 2015 - 2017
|
261 homes
No reviews yet
![The Seasons at Elwood]()
$800Ks
- $900Ks
The Seasons at Elwood, East Northport, NY
Resale Only
|
55+ age-restricted
|
Built 2018 - 2020
|
256 homes
No reviews yet
![Meadow Brook Estates]()
$500Ks
- $500Ks
Meadow Brook Estates, Oxford, CT
Resale Only
|
55+ age-restricted
|
Built 2003 - 2020
|
246 homes
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
5 rating (1 reviews)
![Encore Atlantic Shores]()
$600Ks
- $700Ks
Encore Atlantic Shores, Eastport, NY
Resale Only
|
55+ age-restricted
|
Built 2004 - 2011
|
240 homes
No reviews yet
![The Summit at Bethel]()
$600Ks
- $600Ks
The Summit at Bethel, Bethel, CT
Resale Only
|
55+ age-restricted
|
Built 2010 - 2021
|
235 homes
4.9 rating (14 reviews)
![Chatfield Farms]()
$500Ks
- $500Ks
Chatfield Farms, Beacon Falls, CT
New Construction
|
55+ age-restricted
|
Built 2014 - present
|
231 homes
5 rating (1 reviews)
![Encore at Lake Grove]()
$500Ks
- $600Ks
Encore at Lake Grove, Lake Grove, NY
Resale Only
|
55+ age-restricted
|
Built 2006 - 2007
|
228 homes
No reviews yet
![Woodridge Strathmore Terr...]()
$400Ks
- $400Ks
Woodridge Strathmore Terr..., Mount Sinai, NY
Resale Only
|
55+ age-restricted
|
Built 1974 - 1985
|
226 homes
Want to learn more about 55+ communities in Cheshire?
55places can help!
Questions? Call us:
(475) 244-9781
5 rating (1 reviews)
![Sunrise Village]()
$400Ks
- $400Ks
Sunrise Village, Sayville, NY
Resale Only
|
55+ age-restricted
|
Built 1985 - 1990
|
213 homes
No reviews yet
![Saddle Lakes]()
$400Ks
- $400Ks
Saddle Lakes, Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2000 - 2002
|
196 homes
No reviews yet
![Country Village Estates]()
$400Ks
- $500Ks
Country Village Estates, Coram, NY
Resale Only
|
55+ age-restricted
|
Built 1993 - 2001
|
195 homes
5 rating (1 reviews)
![Sunken Pond Estates]()
$400Ks
- $500Ks
Sunken Pond Estates, Riverhead, NY
Resale Only
|
55+ age-restricted
|
Built 2003 - 2005
|
194 homes
5 rating (1 reviews)
![Westhampton Pines]()
$900Ks
- $1Ms
Westhampton Pines, Westhampton, NY
Resale Only
|
55+ age-restricted
|
Built 2005 - 2013
|
189 homes
Leisure Village
![423 WOODBRIDGE D, BROOKHAVEN, NY, 11961, Brookhaven, NY 11961]()
1 beds
|1 baths
|782 sq ft
|Condo
423 WOODBRIDGE D, BROOKHAVEN, NY, 11961
Community: Leisure Village
MLS 802268 • Douglas Elliman Real Estate, Thomas ...
Leisure Village
![411A WEYMOUTH CT # 411A, RIDGE, NY, 1196..., Ridge, NY 11961]()
2 beds
|1 baths
|1,000 sq ft
|Condo
411A WEYMOUTH CT # 411A, RIDGE, NY, 1196...
Community: Leisure Village
MLS 867323 • Leisure Living Realty Inc, Laura Ruh...
The Bel Aire at East Meadow
![50 MERRICK AVE 307, EAST MEADOW, NY, 115..., East Meadow, NY 11554]()
2 beds
|2 baths
|1,017 sq ft
|Condo
50 MERRICK AVE 307, EAST MEADOW, NY, 115...
Community: The Bel Aire at East Meadow
MLS 897428 • Coldwell Banker American Homes, Evan...
Leisure Village
![156 FALMOUTH CT B, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,085 sq ft
|Condo
156 FALMOUTH CT B, RIDGE, NY, 11961
Community: Leisure Village
MLS 896917 • Signature Premier Properties, Janice...
Leisure Village
![369B WOODBRIDGE DR 55+, BROOKHAVEN, NY, ..., Brookhaven, NY 11961]()
2 beds
|1 baths
|975 sq ft
|Condo
369B WOODBRIDGE DR 55+, BROOKHAVEN, NY, ...
Community: Leisure Village
MLS 883073 • Leisure Living Realty Inc, Laura Ruh...
Want to learn more about 55+ communities in Cheshire?
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Questions? Call us:
(475) 244-9781
Country Village Estates
![36 THEODORE DR, CORAM, NY, 11727, Coram, NY 11727]()
2 beds
|2 baths
|1,186 sq ft
|Condo
36 THEODORE DR, CORAM, NY, 11727
Community: Country Village Estates
MLS 842034 • Coldwell Banker American Homes, Ange...
Leisure Village
![137 EASTBOURNE CT B, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|836 sq ft
|Condo
137 EASTBOURNE CT B, RIDGE, NY, 11961
Community: Leisure Village
MLS 892549 • Bon Anno Realty ERA Powered, Nichola...
Meadowbrook Pointe Athletic Club & Spa
![481 PACING WAY, WESTBURY, NY, 11590, Westbury, NY 11590]()
2 beds
|3 baths
|2,800 sq ft
|Condo
481 PACING WAY, WESTBURY, NY, 11590
Community: Meadowbrook Pointe Athletic Club & Spa
MLS 891184 • Real Broker NY LLC, Matthew J. Lenne...
Jefferson Village
![84 MOLLY PITCHER LN H, YORKTOWN HEIGHTS,..., Yorktown Heights, NY 10598]()
2 beds
|2 baths
|1,100 sq ft
|Condo
84 MOLLY PITCHER LN H, YORKTOWN HEIGHTS,...
Community: Jefferson Village
MLS 877595 • Coldwell Banker Realty, Maureen Conn...
The Waterways at Moriches
![107 E MIDLAND POND CT, MORICHES, NY, 119..., Moriches, NY 11955]()
2 beds
|2 baths
|2,141 sq ft
|Condo
107 E MIDLAND POND CT, MORICHES, NY, 119...
Community: The Waterways at Moriches
MLS 829455 • Douglas Elliman Real Estate, Jo Ann ...
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
The Waterways at Moriches
![497 OAK BLUFF CT, MORICHES, NY, 11955, Moriches, NY 11955]()
2 beds
|3 baths
|1,988 sq ft
|Condo
497 OAK BLUFF CT, MORICHES, NY, 11955
Community: The Waterways at Moriches
MLS 873131 • Signature Premier Properties, Dorrie...
Leisure Village
![273 BERWICK CT B, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 885024 • Pinpoint Realty LI, Marc V. Kaplan
Strathmore Gate East
![9 FORGE LN, CORAM, NY, 11727, Coram, NY 11727]()
MLS 871943 • New Door Properties LLC, Gerald Wood
Heritage Hills
![682 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589]()
3 beds
|2 baths
|2,030 sq ft
|Condo
682 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
MLS 891807 • Houlihan Lawrence Inc., Donna O'Conn...
Leisure Glen
![293 GLEN DR, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 894371 • Howard Hanna Coach, Kalliopi C. Suar...
Want to learn more about 55+ communities in Cheshire?
55places can help!
Questions? Call us:
(475) 244-9781
HarborView
![100 HARBOR VIEW DR 249, PORT WASHINGTON,..., Port Washington, NY 11050]()
2 beds
|3 baths
|1,493 sq ft
|Condo
100 HARBOR VIEW DR 249, PORT WASHINGTON,...
Community: HarborView
MLS 840770 • Douglas Elliman Real Estate, Melanie...
Heritage Hills
![15 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589]()
2 beds
|2 baths
|1,139 sq ft
|Condo
15 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
MLS 891829 • Howard Hanna Rand Realty, Theresa A....
Leisure Village
![404B WOODBRIDGE DR 404B, BROOKHAVEN, NY,..., Brookhaven, NY 11961]()
2 beds
|1 baths
|907 sq ft
|Condo
404B WOODBRIDGE DR 404B, BROOKHAVEN, NY,...
Community: Leisure Village
MLS 867426 • Leisure Living Realty Inc, Laura Ruh...
Leisure Village
![164 FALMOUTH CT E, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 893757 • Douglas Elliman Real Estate, Joseph ...
Stoneleigh Woods at Carmel
![206 EGRETS LANDING, CARMEL, NY, 10512, Carmel, NY 10512]()
2 beds
|2 baths
|1,492 sq ft
|Condo
206 EGRETS LANDING, CARMEL, NY, 10512
Community: Stoneleigh Woods at Carmel
MLS 893569 • Weichert Realtors, Tremaine Selby
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Jefferson Village
![156 CARRIAGE CT G, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598]()
1 beds
|1 baths
|850 sq ft
|Condo
156 CARRIAGE CT G, YORKTOWN HEIGHTS, NY,...
Community: Jefferson Village
MLS 823393 • Houlihan Lawrence Inc., Nancy Kenned...
Fairfield at St. James
![302 GOTHAM WAY, SAINT JAMES, NY, 11780, Saint James, NY 11780]()
3 beds
|3 baths
|1,548 sq ft
|Townhouse
302 GOTHAM WAY, SAINT JAMES, NY, 11780
Community: Fairfield at St. James
MLS 874456 • Signature Premier Properties, Anthon...
Kensington Estates
![46 PLAINVIEW RD, WOODBURY, NY, 11797, Woodbury, NY 11797]()
6 beds
|5 baths
|4,333 sq ft
|House
46 PLAINVIEW RD, WOODBURY, NY, 11797
Community: Kensington Estates
MLS 886291 • SRG Residential LLC, Jared Sarney
Breton Hills
![308 BRETON WAY # 308, GLEN COVE, NY, 115..., Glen Cove, NY 11542]()
2 beds
|2 baths
|1,500 sq ft
|Condo
308 BRETON WAY # 308, GLEN COVE, NY, 115...
Community: Breton Hills
MLS 862280 • Goldilocks Real Estate, Holly Gottli...
Country Village Estates
![11 THEODORE DR, CORAM, NY, 11727, Coram, NY 11727]()
2 beds
|2 baths
|1,386 sq ft
|Condo
11 THEODORE DR, CORAM, NY, 11727
Community: Country Village Estates
MLS 848469 • Signature Premier Properties, Lori S...
Want to learn more about 55+ communities in Cheshire?
55places can help!
Questions? Call us:
(475) 244-9781
Fairfield at St. James
![914 FENWAY RD, SAINT JAMES, NY, 11780, Saint James, NY 11780]()
2 beds
|2 baths
|1,200 sq ft
|Condo
914 FENWAY RD, SAINT JAMES, NY, 11780
Community: Fairfield at St. James
MLS 886931 • Douglas Elliman Real Estate, Laura R...
Stone Ridge Estates
![156 CHRISTINE DR, DIX HILLS, NY, 11746, Dix Hills, NY 11746]()
2 beds
|2 baths
|1,700 sq ft
|Condo
156 CHRISTINE DR, DIX HILLS, NY, 11746
Community: Stone Ridge Estates
MLS 859377 • Howard Hanna Coach, Susan Catik
Jefferson Village
![6 DEVON CT B, YORKTOWN HEIGHTS, NY, 1059..., Yorktown Heights, NY 10598]()
2 beds
|1 baths
|1,000 sq ft
|Condo
6 DEVON CT B, YORKTOWN HEIGHTS, NY, 1059...
Community: Jefferson Village
MLS 865906 • Keller Williams Realty Partner, Rose...
The Waterways at Moriches
![414 LINDSAY LN, MORICHES, NY, 11955, Moriches, NY 11955]()
2 beds
|2 baths
|2,141 sq ft
|Condo
414 LINDSAY LN, MORICHES, NY, 11955
Community: The Waterways at Moriches
MLS 835585 • Realty Connect USA LLC, Roseann Bisc...
Greenwood Village
![77 VILLAGE CIR, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|1 baths
|1,000 sq ft
|Condo
77 VILLAGE CIR, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 853523 • Gateway to The Hamptons R E, Janet R...
Download the Ultimate 55+ Homebuying Guide
Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Leisure Village
![269 BERWICK CT B, RIDGE, NY, 11961, Ridge, NY 11961]()
2 beds
|1 baths
|1,048 sq ft
|Condo
269 BERWICK CT B, RIDGE, NY, 11961
Community: Leisure Village
MLS 856130 • Oversouth LLC, Deniz Ozgur
Jefferson Village
![27 WALDEN CT APT A A, YORKTOWN HEIGHTS, ..., Yorktown Heights, NY 10598]()
|
1 baths
|550 sq ft
|Condo
27 WALDEN CT APT A A, YORKTOWN HEIGHTS, ...
Community: Jefferson Village
MLS 888092 • Prime Site Realty Exq Homes, Luigi L...
Greenwood Village
![21 LIMETREE DR, MANORVILLE, NY, 11949, Manorville, NY 11949]()
2 beds
|2 baths
|1,100 sq ft
|Condo
21 LIMETREE DR, MANORVILLE, NY, 11949
Community: Greenwood Village
MLS 866101 • Signature Premier Properties, Meliss...
Leisure Village
![192 VENTRY CT A, RIDGE, NY, 11961, Ridge, NY 11961]()
MLS 867626 • Realty One Group First, Magdalena Ko...
Vineyards at Moriches
![4 TONI CT, CENTER MORICHES, NY, 11934, Center Moriches, NY 11934]()
2 beds
|3 baths
|2,196 sq ft
|Condo
4 TONI CT, CENTER MORICHES, NY, 11934
Community: Vineyards at Moriches
MLS 883128 • Points East Real Estate, David L. Ra...
Want to learn more about 55+ communities in Cheshire?
55places can help!
Questions? Call us:
(475) 244-9781
HarborView
![100 HARBOR VIEW DR APT 515, PORT WASHING..., Port Washington, NY 11050]()
2 beds
|3 baths
|1,495 sq ft
|Condo
100 HARBOR VIEW DR APT 515, PORT WASHING...
Community: HarborView
MLS 864376 • Daniel Gale Sothebys Intl Rlty, Mary...
The Waterways at Moriches
![521 HIGHLAND CT # 521, MORICHES, NY, 119..., Moriches, NY 11955]()
2 beds
|2 baths
|1,839 sq ft
|Condo
521 HIGHLAND CT # 521, MORICHES, NY, 119...
Community: The Waterways at Moriches
MLS 838254 • Douglas Elliman Real Estate, Jo Ann ...
The Waterways at Moriches
![279 DOCKSIDE CT, MORICHES, NY, 11955, Moriches, NY 11955]()
2 beds
|2 baths
|1,480 sq ft
|Condo
279 DOCKSIDE CT, MORICHES, NY, 11955
Community: The Waterways at Moriches
MLS 877043 • Douglas Elliman Real Estate, Jo Ann ...
The Waterways at Moriches
![106 E MIDLAND POND CT # 1, MORICHES, NY,..., Moriches, NY 11955]()
2 beds
|2 baths
|1,982 sq ft
|Condo
106 E MIDLAND POND CT # 1, MORICHES, NY,...
Community: The Waterways at Moriches
MLS 859359 • Douglas Elliman Real Estate, Loukia ...
Plymouth Estates at Mount Sinai
![166 IRA RD, MOUNT SINAI, NY, 11766, Mount Sinai, NY 11766]()
2 beds
|2 baths
|1,820 sq ft
|Townhouse
166 IRA RD, MOUNT SINAI, NY, 11766
Community: Plymouth Estates at Mount Sinai
MLS 878423 • Aliano Real Estate, Nicholas A. Colo...
Frequently Asked Questions
In Cheshire, there is 1 small community with less than 500 homes.
The smallest 55+ community in Cheshire has 88 homes, the largest has 88 homes, and the average community consists of 88 homes.
No, there are no gated 55+ communities in Cheshire.
Want more information about active adult communities around Cheshire?
Want to learn more about 55+ communities in Cheshire?
290
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near Cheshire
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